Copper-Mediated One-Pot Access to Benzo[b][1,4]thiazines from 2-N-Sulfonylaminoaryl Disulfides

被引：6

作者：

Viglianisi, Caterina ^{[1
]}

Bonaccorsi, Paola ^{[2
]}

Simone, Lavinia ^{[1
]}

Nassini, Lucia ^{[1
]}

Menichetti, Stefano ^{[1
]}

机构：

[1] Polo Sci & Tecnol Univ Firenze, Dipartimento Chim Ugo Schiff, I-50019 Sesto Fiorentino, Italy

[2] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 09期

关键词：

Synthetic methods; Disulfides; Sulfur heterocycles; Copper; Cycloaddition; DIELS-ALDER REACTION; ANTIOXIDANT ACTIVITY; DERIVATIVES; SULFUR;

D O I：

10.1002/ejoc.201200023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-N-Sulfonylaminoaryl disulfides can be converted into the corresponding benzo[b][1,4]thiazines in one pot when reacted with an electron-rich alkene in the presence of a base and a substoichiometric amount of a copper salt. Depending upon the reaction conditions, and in particular the copper salt used, we observed the concurrent formation of variable amounts of the corresponding benzo[b][1,4]thiazine S-oxides that are not the result of a post-oxidation reaction. The overall procedure can provide simple access to benzo[b]thiazines or thiazine S,S-dioxides by sequential reduction or oxidation of the crude reaction mixtures.

引用

页码：1707 / 1711

页数：5

共 21 条

[1] Effect of ortho-SR groups on O-H bond strength and H-atom donating ability of phenols:: A possible role for the tyr-cys link in galactose oxidase active site? [J].

Amorati, Riccardo ;

Catarzi, Francesca ;

Menichetti, Stefano ;

Pedulli, Gian Franco ;

Viglianisi, Caterina .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) :237-244

[2] Kinetic and thermochemical study of the antioxidant activity of sulfur-containing analogues of vitamin E [J].

Amorati, Riccardo ;

Cavalli, Andrea ;

Fumo, Maria Grazia ;

Masetti, Matteo ;

Menichetti, Stefano ;

Pagliuca, Chiara ;

Pedulli, Gian Franco ;

Viglianisi, Caterina .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (29) :8223-8230

[3]

[Anonymous], 2003, Angew. Chem, DOI DOI 10.1002/ANGE.200300573

[4] Cu-Catalyzed Efficient Synthetic Methodology for Ebselen and Related Se-N Heterocycles [J].

Balkrishna, Shah Jaimin ;

Bhakuni, Bhagat Singh ;

Chopra, Deepak ;

Kumar, Sangit .

ORGANIC LETTERS, 2010, 12 (23) :5394-5397

[5] Synthesis of benzo[b] [1,4]thiazines by hetero-Diels-Alder reaction of o-iminothioquinones [J].

Campo, Margherita ;

Lamanna, Giuseppe ;

Menichetti, Stefano .

SYNLETT, 2007, (19) :2961-2964

[6] alpha-oxosulfines .1. Reactivity of alpha-oxosulfines obtained from Retro Diels-Alder reaction of 1,4-oxathiin-S-oxides. [J].

Capozzi, G ;

Fratini, P ;

Menichetti, S ;

Nativi, C .

TETRAHEDRON, 1996, 52 (37) :12233-12246

[7] Highly potent 1,4-benzothiazine derivatives as KATP-channel openers [J].

Cecchetti, V ;

Calderone, V ;

Tabarrini, O ;

Sabatini, S ;

Filipponi, E ;

Testai, L ;

Spogli, R ;

Martinotti, E ;

Fravolini, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (17) :3670-3679

[8] [2+4] and [4+2] cycloadditions of o-thioquinones with 1,3-dienes: A computational study [J].

Contini, Alessandro ;

Leone, Samantha ;

Menichetti, Stefano ;

Viglianisi, Caterina ;

Trimarco, Pasqualina .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15) :5507-5514

[9] An o-iminothioquinone:: Its cycloaddition to produce an indologlycoside and its self-dimerization to form a dithio-diazocycloctane, the structure assignment of which is based on the DFT prediction of its IR spectrum [J].

Diep, V ;

Dannenberg, JJ ;

Franck, RW .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7907-7910

[10] Copper-catalyzed direct thiolation of benzoxazole with diaryl disulfides and aryl thiols [J].

Fukuzawa, Shin-ichi ;

Shimizu, Eiji ;

Atsuumi, Yuka ;

Haga, Masatake ;

Ogata, Kenichi .

TETRAHEDRON LETTERS, 2009, 50 (20) :2374-2376

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